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Chester VT Real Estate

Located in Windsor County, Chester is a wonderful New England town reminiscent of a bygone era. With architecture pre-dating the civil war, Chester is rich in history and beauty. Although historic, the quaint town is thriving with its unique markets, galleries, and restaurants that offer much to do. The town is also conveniently located close to Okemo Mountain and Mount Snow for those who enjoy outdoor recreation as well as within driving distance to Manchester, VT

Search the latest real estate in Chester, VT with Maple Sweet Real Estate. Find the right property for you from a variety of listings. To save your favorites, register with us and you can get email notifications when similar properties are posted. Already have an account with us? Log in here.

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465 Pennell Road Chester VT 05143

Chester, VT465 Pennell Road

Price$1,685,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4918189

  • Residential Single Family
  • Square Feet 4,444
  • Bedrooms 4
  • Construction Existing
  • Bathroom 5

This extraordinary residence and property is located in the vibrant community of Chester. Chester is easily accessed from Interstate 91 and is the gateway to Vermonts best ski areas which create an abundance of exceptional restaurants, cultural events and recreational options. The property is a south facing, very private 79 acres which consists of well maintained woodlands including a sugarbush with a state of the art sugarhouse and open meadows in the forefront of long range views. Located just below the residence is a large swimming, fishing pond with an adjacent lighted tennis court. Trails for hiking, cross country skiing and mountain biking are throughout the property. Truly an exceptional private setting that has been enhanced by the residence which is expertly sited to take in all that the property offers. The residence was designed and built by the owner who is a renowned wood craftsman. The level of craftsmanship displayed throughout the house is without equal. The choicest woods combined with incredible execution make for a truly unique environment. Every room and space in the house is warm and inviting while offering efficiency and sustainability. Combine this with state of the art systems and unexpected amenities including an adult sized and scaled treehouse make this property a must see for the discerning buyer. You won't be disappointed.

Listed by Wade Treadway of Wade I Treadway Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

141 Stage Road Chester VT 05143

Chester, VT141 Stage Road

Price$924,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4822981

  • Land
  • Area Near Skiing, Rural
  • Acreage 509.73
  • Utilities None
  • Zoning Residential

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 509+/- acres has it all. Made up of 4 contiguous preexisting lots the parcel has road frontage on Stage Road in Chester giving multiple opportunities for a number of small subdivisions. Three lots also front onto route 35 between Chester and Grafton which includes two 70 +/- acres lots. There are also gravel deposits on the site which could be used to develop the logging trails further. If you have conservation on your mind the entire lot is enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded and hosts a large open area for staging a logging operation. There are also a network of marked logging trails throughout the property making it easily accessible. The beautifully crafted ponds offer a welcome spot to take in the beauty of the landscape as well attracting all manner of wildlife. The seller will entertain selling individual lots separately. Whether you wish to develop or keep this pristine site as is you will find endless choices and opportunity for this very special place. Come see today!!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

374 Richardson Road Chester VT 05143

Chester, VT374 Richardson Road

Price$699,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4908861

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,776
  • Bathroom 2
  • Bedrooms 3

Gracefully settled between the villages of Chester and Londonderry, sits a Vermont Farmhouse at road's end, sited on eleven+ acres of wood'n meadow. Dotted with old stone walls, a wildlife pond and enchanting views. The setting is magical. A wide country porch invites rocking chairs and visitors while the screened area encourages outdoor entertaining much of the year. The vintage flavor is apparent throughout the home- opening panel doors with antique latches or stepping foot on wide wood floors milled from indigenous trees from decades ago. This location is central to recreating: ski, hike, snowmobile, swim, or enjoy our local restaurants, theater and shopping. A center island kitchen with breakfast nook overlooks the rolling meadows and glass doors allows life to spill over onto the porch, deck or firepit area. A traditional dining room, adjacent to the intimate living room, awaits memorable dinner parties. The great room's remarkable soaring ceiling creates a central gathering spot and includes a cast iron wood burning stove to warm by when winter is settling in and snow abounds . The main floor bedroom would also make a delightful home office overlooking the fields to the rear. Upstairs you'll find additional bedrooms including a large “beamed ceiling” primary and a fun multi-functional den/game room. Two sets of farmhouse stairs give easy access. If quiet and open and vintage is your desire..Look no further. Showings begin Thursday, May 12th. Owner is a licensed Realtor.

Listed by Lavinia Lee Brown and Nancy Jensen of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

166 North Street Chester VT 05143

Chester, VT166 North Street

Price$695,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4923376

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 3,744

Unique opportunity to own a piece of history. This six-bedroom, five and a half-bath home on .67 acres is nestled in the heart of the historic stone village. Chester's stone village is currently recognized by the United States Department of Interior as perhaps one of the only stone villages in the country. This two-story federal-style stone home offers many opportunities with its spacious floor plan. Enjoy flexibility with an accessory apartment above and fully renovated owner's quarters below. Walk the grounds to enjoy the patio with its own stone cottage that is currently used to make maple kettle corn. Cross the garden bridge on your way to the lily pond or enjoy the shade from one of the fruit trees. The property offers the best of both worlds with a sprawling backyard yet conveniently located to restaurants and shopping. Okemo Resort and the lakes region are just a quick 12 miles away. This location offers lots to do each season including festivals, the Weston Playhouse, concerts, and much much more. Taxes are based on current town assessment.

Listed by Katherine Burns of William Raveis Vermont Properties

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

7 Pine View Drive Chester VT 05143

Chester, VT7 Pine View Drive

Price$580,000The price has recently decreased

MLS Number 4908570

  • Commercial
  • Year Built 2006
  • Square Feet 3,164
  • Acreage 1.56

Excellent opportunity presents itself with this outstanding commercial property located on Route 103 Chester. High volume traffic and exposure gives this property unlimited potential for the entrepreneur buyer. This exceptional post and beam structure sits on 1.56 acres and was built in 2006. Currently used as office space, it had been a retail shop, gallery and cafe in the past. Mixed use zoning allows for a future residential possibility. Over 3,000 usable square feet, ample parking, radiant heat, gorgeous tile flooring, natural wood beams. Town water and septic hooked up to the town line. Bring your vision and energy and create your dream.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

12 Common Street Chester VT 05143

Chester, VT12 Common Street

Price$525,000The price has recently decreased

MLS Number 4928621

  • Commercial
  • Year Built 1820
  • Square Feet 4,060
  • Acreage 0.25

Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential! The first being the business store front, second is a space in the back which could easily be turned into a rental with a kitchen and separate bathroom, the third is a second floor 2 bedroom 1 bathroom with much potential! Along with the many benefits of this properties location comes parking right on the Green. Some recent updates are the back portion on the building has a new roof and solar was added recently as well.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

12 Common Street Chester VT 05143

Chester, VT12 Common Street

Price$525,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4929151

  • Multifamily
  • Square Feet 4,060
  • Bathroom 2
  • Units 3
  • Acreage 0.25

Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential! The first being the business store front, second is a space in the back which could easily be turned into a rental with a kitchen and separate bathroom, the third is a second floor 2 bedroom 1 bathroom with much potential! Along with the many benefits of this properties location comes parking right on the Green. Some recent updates are the back portion on the building has a new roof and solar was added recently as well.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

95 Church Street Chester VT 05143

Chester, VT95 Church Street

Price$495,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4927983

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 2
  • Construction Existing
  • Square Feet 2,794

Welcome to 95 Church St in the charming town of Chester. This 1800's home has seen many changes over the years including most recently a whole house renovation. This is a great property for someone that loves the charming features of an older home but in turn key condition. Renovations include but are definitely not limited to the kitchen, bathrooms, flooring, windows, heating systems including in floor radiant heat, siding, electrical, pex plumbing, spray foam insulation, and a new standing seam roof. The kitchen features beautiful hand made cherry cabinets with custom pantry cabinets as well. While we are talking about cabinets the walk-in closet features walnut shelving and drawers. The floors throughout most of the home are a beautiful hickory. In addition to the the two bathrooms there is an en suite bathroom that is ruffed in and waiting for your final touches. Sit back and enjoy the village location from the screened in porch or patio.

Listed by Katherine Burns of William Raveis Vermont Properties

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

498 Marcs Drive Chester VT 05143

Chester, VT498 Marcs Drive

Price$490,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4924119

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,564
  • Bathroom 3
  • Bedrooms 4

Welcome to Vermont living! This spacious, well-kept home has lots of room for your family, pets, and even an RV in the oversized garage! Situated on over 2.5 acres, there is plenty of privacy. The beautiful yard includes raised beds for veggies or flowers as well as a fenced in area for your animals to stay safe. Located just outside the village of Chester, this home is within 30 minutes to several ski areas. There is a hospital just 15 minutes away as well as grocery and restaurants. Access to VAST trail system right from Marcs Drive. The home is filled with lots of natural wood along with plenty of windows. Downstairs you'll find a large master with an en-suite bath and two closets. The master has a radiant heat floor. The laundry room is also conveniently located on the lower level. Upstairs the three bedrooms and a bath offer plenty of space for the family. Over the garage is an office, and in the basement there's a big bonus room with a walkout into the yard. High speed fiber internet is installed; perfect to work from home. Some of the recent improvements include: paving the driveway; installing a split pump (a/c - heat), staining the house, a new well pump, and installing a bay window. This home has three heating systems and is wired for and includes a portable generator. There isn't much to do here except move in!

Listed by Heather Gleim of Walnut Hill Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

81 Main Street Chester VT 05143

Chester, VT81 Main Street

Price$479,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4929143

  • Residential Single Family
  • Bathroom 4
  • Construction Existing
  • Bedrooms 5
  • Square Feet 3,864

Welcome to 81 Main Street! Built in 1820 and located in the heart of the Chester village, this property is historically known as the Guy Earle House and has been a year round vacation home and short term rental property. This quintessential VT gem on .44 acres+/- features 5 bedrooms and 4 baths. Among it's many attractive features are a large living room with wood burning fireplace, formal dining room, two first floor bedrooms, one en suite and an additional bathroom. The 2nd floor includes a large living area, en suite bedrooms, a bonus game room with a handsome wet bar, hand-crafted from school benches. and a pellet stove. Additional Features include: first floor laundry, mudroom/workshop and unfinished attic space. The double lot has generous parking, an oversized 1 car detached garage with potential space to be finished and a separate shed for gardening in the large level yard. The 4 porches adorning the house offer outdoor covered gathering spaces. Stroll to the green for coffee and browse the shops. Close to 5 ski areas, recreational activities and year round fun!

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3778 Trebo Road Chester VT 05142

Chester, VT3778 Trebo Road

Price$429,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4924795

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,456
  • Construction Existing

This immaculately maintained home was built in 2013 and is situated on over 23 acres with a pond and oversized 3-car garage! Enjoy privacy and solitude with plenty of room to garden, hike, cross country ski or snowshoe without ever leaving your own property. If motorized fun is more your style, there is ample indoor storage space for snowmobiles, boats or ATV's. When at full capacity the pond is 12 feet with a sandy "beach" area. Add a floating swim platform for summer fun or enjoy the peaceful spot with a fire in the large stone hearth pond side. The home itself is bright and cheery with open concept living spaces that open to either the front deck or back deck and patio spaces for a great indoor/outdoor flow. Primary suite with large full bath, double sinks, soaking tub, and additional shower. On the other end of the home are a guest bedroom and den with an additional full bath. Also on the main floor is a spacious and functional mud room with a utility sink and full laundry. If you need more space, the full basement is clean with large windows, high ceilings and could be finished to suit. Heated garage w/3 large bays, workshop space and full second floor for recreation, office space, or could be finished for more living area. If you do find yourself out and about there is plenty to do nearby. Okemo Resort is only 12 miles away and downtown Chester boasts many boutique shops, restaurants, yoga, and art studios, farmers' market and more! Showings begin Sunday Aug 14.

Listed by Jacki Murano of Southern Vermont Realty Group

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

538 Clemons Road Chester VT 05143

Chester, VT538 Clemons Road

Price$410,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 4919284

  • Residential Single Family
  • Bathroom 3
  • Bedrooms 3
  • Construction Existing
  • Square Feet 1,900

All the possibilities! Prime location, desirable size, level secluded lawn, oversized three bay garage with ample storage...the list goes on and on. Enter through the attached garage and into the wonderful mudroom to find yourself comfortably moving around the open floor plan. This well maintained home is ready for all of your ideas and plans. Let's talk about the garage! Built with big ideas in mind, this building can house all of your toys and equipment. Equipped with oversized doors and one drive-through bay. The office area and upstairs storage space offer endless possibilities. This building is a huge bonus. The location is spectacular, complete with a beautiful fire pit and tons of open space for all of your gardening visions. We can't wait to show you what this property has to offer!

Listed by Chelsea Bevis of KW Vermont Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated September 29, 2022 3:39 AM EDT.

 

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